Diisopropylethylamine → Tert-butyl (2S)-4-{N-[2-(2-{2-[2-(2-{3-(4-hydroxyphenyl)-5-[(N-morpholin-4-ylcarbamoyl)amino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetylamino)ethoxy]ethoxy}ethoxy) ethyl]carbamoyl}-2-{[4-(methylamino)phenyl]carbonylamino}butanoate

HRID 720870노트

반응식

HRID 720870 반응식
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([OH:16])=O)[N:11]=[C:10]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([NH:25][C:26]([NH:28][N:29]5[CH2:34][CH2:33][O:32][CH2:31][CH2:30]5)=[O:27])[C:22]=4[C:23](=[O:24])[C:9]=23)=[CH:4][CH:3]=1.[NH2:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][NH:47][C:48]([CH2:50][CH2:51][C@H:52]([NH:60][C:61]([C:63]1[CH:68]=[CH:67][C:66]([N:69](C(OCC2C=CC=CC=2)=O)[CH3:70])=[CH:65][CH:64]=1)=[O:62])[C:53]([O:55][C:56]([CH3:59])([CH3:58])[CH3:57])=[O:54])=[O:49].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([NH:35][CH2:36][CH2:37][O:38][CH2:39][CH2:40][O:41][CH2:42][CH2:43][O:44][CH2:45][CH2:46][NH:47][C:48]([CH2:50][CH2:51][C@H:52]([NH:60][C:61]([C:63]3[CH:64]=[CH:65][C:66]([NH:69][CH3:70])=[CH:67][CH:68]=3)=[O:62])[C:53]([O:55][C:56]([CH3:57])([CH3:58])[CH3:59])=[O:54])=[O:49])=[O:16])[N:11]=[C:10]3[C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([NH:25][C:26](=[O:27])[NH:28][N:29]5[CH2:30][CH2:31][O:32][CH2:33][CH2:34]5)[C:22]=4[C:23](=[O:24])[C:9]=23)=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66910315HCID 66910315, 화합물HCID 1357740212-{3-(4-Hydroxyphenyl)-5-[(morpholin-4-ylamino)carbonylamino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetic acid

생성물 1

HCID 136397846Tert-butyl (2S)-4-{N-[2-(2-{2-[2-(2-{3-(4-hydroxyphenyl)-5-[(N-morpholin-4-ylcarbamoyl)amino]-4-oxoindeno[3,2-c]pyrazol-2-yl}acetylamino)ethoxy]ethoxy}ethoxy) ethyl]carbamoyl}-2-{[4-(methylamino)phenyl]carbonylamino}butanoate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Compound 38 (0.52 g, 1.1 mmol) and compound 12 (0.55 g, 1.1 mmol) were dissolved in DMF and HBTU (0.8 g, 2.1 mmol) was added as a solid followed by DIEA (0.52 ml, 3 mmol). The reaction mixture was stirred at room temperature overnight, diluted with EtOAc and the organic phase washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated to an oil. This oil was purified by flash silica chromatography (1 to 2 to 3 to 4 to 5% MeOH/CH2Cl2) to give a yellow foam (0.45 g, 0.47 mmol, 43%, compound 39).

후처리

  1. washthe organic phase washed with saturated NaHCO3, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to an oil
  5. customThis oil was purified by flash silica chromatography (1 to 2 to 3 to 4 to 5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-33fd9d67442c41eb91158edb629cc688
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135550B2

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